(-)-Bornyl chloride

Base Information

• Chemical Name: (-)-Bornyl chloride
• CAS No.: 33602-15-2
• Molecular Formula: C₁₀H₁₇Cl
• Molecular Weight: 172.698
• UNII: 5NUA53V7U0
• Nikkaji Number: J818.250G
• Wikidata: Q27262606
• Mol file: 33602-15-2.mol

Synonyms:(-)-Bornyl chloride;Bornyl chloride, (-)-;Bornane, 2-chloro-, endo-(-)-;UNII-5NUA53V7U0;2-Endo-bornyl chloride, endo-(-)-;5NUA53V7U0;33602-15-2;Bicyclo(2.2.1)heptane, 2-chloro-1,7,7-trimethyl-, (1S,2R,4S)-;Pinenhydrochlorid;SCHEMBL16691957;NS00043637;Q27262606

Chemical Property of (-)-Bornyl chloride

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 172.1018782
• Heavy Atom Count: 11
• Complexity: 185

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C2CCC1(C(C2)Cl)C)C
• Isomeric SMILES: C[C@]12CC[C@H](C1(C)C)C[C@H]2Cl

Technology Process of (-)-Bornyl chloride

There total 60 articles about (-)-Bornyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 20.0%

camphene (79-92-5) + 3,3-dimethyl-allyl chloride (503-60-6) → bornyl chloride (464-41-5,559-45-5,6120-13-4,27720-69-0,30462-53-4,33602-15-2,73804-39-4,91547-96-5) + 4-methyl-1-(3',3'-dimethylbicyclo<2.2.1>hept-2-ylidene)pent-2-ene (116877-32-8) + (E)-isosantalene (63028-14-8) + 5-(1-chloro-1-methyl-ethyl)-2-methyl-7-(3',3'-dimethylbicyclo<2.2.1>hept-2-ylidene)hept-2-ene (116877-33-9,116948-00-6)

Guidance literature:

With zinc(II) chloride; In diethyl ether; dichloromethane; at -78 ℃; for 18h;

DOI:10.1016/S0040-4020(01)83451-7

Reference yield:

methylmagnesium bromide (75-16-1) → bornyl chloride (464-41-5,559-45-5,6120-13-4,27720-69-0,30462-53-4,33602-15-2,73804-39-4,91547-96-5) + 6endo,6'endo-dichloro-1,7,7,1',7',7'-hexamethyl-[2ξ,2'=x]binorbornyl

Guidance literature:

With diethyl ether; cobalt(II) chloride;

DOI:10.1021/ja01603a061

Reference yield:

→ bornyl chloride (464-41-5,559-45-5,6120-13-4,27720-69-0,30462-53-4,33602-15-2,73804-39-4,91547-96-5)

Guidance literature:

at 140 - 150 ℃;

upstream raw materials:

methanol

3-chloro-2.2.3-trimethyl-norbornane of uncertain configuration

Pinene

(+)-camphene

Downstream raw materials:

2-endo-chloro-bornane

isobornyl acetate

camphene hydrate

dl-camphene

Refernces

• 1、 Rahman, Azizur,Baeuml, Englbert,Klein, Herbert,Mayr, Herbert. "PRENYLATION OF CAMPHENE - A CARBOCATIONIC ROUTE TO ISOSANTALENE AND ITS DERIVATIVES". . p. 4119 - 4124. Retrieved 2007/10/02.